3,4-dichloro-N-((2r,5r)-2-(2-(6-methoxyquinolin-4-yl)ethyl)-1,3-dioxan-5-yl)benzamide

ID: ALA4756100

PubChem CID: 146503219

Max Phase: Preclinical

Molecular Formula: C23H22Cl2N2O4

Molecular Weight: 461.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2nccc(CC[C@H]3OC[C@H](NC(=O)c4ccc(Cl)c(Cl)c4)CO3)c2c1

Standard InChI:  InChI=1S/C23H22Cl2N2O4/c1-29-17-4-6-21-18(11-17)14(8-9-26-21)3-7-22-30-12-16(13-31-22)27-23(28)15-2-5-19(24)20(25)10-15/h2,4-6,8-11,16,22H,3,7,12-13H2,1H3,(H,27,28)/t16-,22-

Standard InChI Key:  ZCCQPOJAEYPDRY-CIEDQVTBSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   34.5116   -3.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2254   -3.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2226   -2.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5098   -2.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7994   -3.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8017   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0917   -2.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3830   -2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3846   -3.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0912   -3.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6711   -2.1300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5063   -1.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2164   -0.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9300   -1.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9288   -2.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6383   -2.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3508   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3493   -1.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6353   -0.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0587   -2.5278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7704   -2.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4824   -2.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7700   -1.2975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6689   -1.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4808   -3.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1920   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9025   -3.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8974   -2.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1856   -2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6024   -2.1051    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   41.6120   -3.7488    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  8 11  1  0
  4 12  1  0
 12 13  1  0
 14 13  1  1
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  6
 20 21  1  0
 21 22  1  0
 21 23  2  0
 11 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 22  1  0
 28 30  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756100

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 461.35

Molecular Weight (Monoisotopic): 460.0957

AlogP: 4.65

#Rotatable Bonds: 6

Polar Surface Area: 69.68

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.22

CX LogP: 4.60

CX LogD: 4.60

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -0.72

References

1. Lu Y,Papa JL,Nolan S,English A,Seffernick JT,Shkolnikov N,Powell J,Lindert S,Wozniak DJ,Yalowich J,Mitton-Fry MJ.  (2020)  Dioxane-Linked Amide Derivatives as Novel Bacterial Topoisomerase Inhibitors against Gram-Positive Staphylococcus aureus.,  11  (12): [PMID:33335666] [10.1021/acsmedchemlett.0c00428]

Source

Source(1):

• Scientific Literature